


Swimming with the Sharks

by dvrk_dvys



Category: Teen Wolf (TV)
Genre: Alcohol, Alternate Universe - Human, Alternate Universe - Mob, Artist Stiles Stilinski, Bartender Stiles Stilinski, Crimes & Criminals, M/M, Mafia AU, Organized Crime, Sheriff Stilinski's Name is John
Language: English
Status: In-Progress
Published: 2017-06-04
Updated: 2017-10-19
Packaged: 2018-11-09 02:45:28
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 12,842
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11095263
Author URL: https://archiveofourown.org/users/dvrk_dvys/pseuds/dvrk_dvys
Summary: "Now that Stiles had been staring at Derek for so long and could put a name to his face, he could begin to place why he looked so familiar. Stiles had seen him in the local newspapers.And a few surveillance photos from his dad's case files.If Stiles' memory served him correctly, he was standing in front of Derek Hale, crime lord and mob boss of Beacon Hills."





	1. the meeting

**Author's Note:**

> I'm bad at summaries and this is my first fic so it's a double whammy!
> 
> All rights go to Teen Wolf, Jeff Davis, MTV etc. I own nothing. 
> 
> [follow my personal tumblr](http://cursed-kid.tumblr.com)  
> [fandom tumblr](http://hecks-eyebrows.tumblr.com)
> 
>  
> 
> [my beta's tumblr](http://sassyhunters.tumblr.com)

Stiles Stilinski hated his job. On paper, being a bartender at the trendy bar, Triskele, sounded like a dream come true. Working there allowed Stiles' mornings and afternoons free so that he could work on his art, he got discounts on alcohol, _and_ got cash tips. Now, as Stiles not-so-gently thrust his remaining customers' bar tabs in their faces, forty five minutes after last call, he was seriously considering a career change. 

Stiles resumed cleaning the dirty glasses from that night's shift as the remaining customers paid their bills, dropped tips in the tip jar, and presumably arranged for a ride home. After the final customer stumbled out, Stiles sighed in relief and continued cleaning up, lost in thought. 

Stiles moved back to Beacon Hills after receiving the news that his father, the Sheriff, had a massive heart attack on the job. Stiles was on the other side of the country at the time, trying to find work in New York after graduating college with his Bachelor's degree in art. Needless to say, after getting that phone call in the middle of the night, he was on the next flight back to California. 

But that was two months ago and Stiles hadn't planned on staying in Beacon Hills. His father has been getting stronger and stronger by the day, and was slowly getting back to work. But now they had hospital bills to worry about on top of regular bills, and Stiles' student loans. They still hadn't recovered (financially and emotionally) from when Stiles' mother passed and still weren't done paying those bills yet. So, Stiles decided to move back home permanently to help his dad out. Most of his income came from working at the bar, which then went to helping pay off his dad's medical bills (secretly, of course, because the Sheriff was nothing if not stubborn). The rest of his income came from selling his art pieces on the website, Etsy. He made a decent profit from it and he had garnered a small, yet loyal fan base on Tumblr and even got a few shout outs from some local art bloggers. That was great and all, but Stiles wanted more. He missed rubbing elbows with other artists, and he fantasized about attending art shows and sipping champagne while giving pretentious reviews of art amongst his college friends. 

God, he missed New York. 

Stiles was disturbed from his reverie by the sound of the front door opening and closing. He had moved to the storage room during his daydream to take the bottles that needed restocking up to the front so he wouldn't have to waste time doing it tomorrow during his shift. 

Stiles was immediately on high alert. Beacon Hills had garnered a violent reputation in the past few years. And the last thing Stiles needed now was for someone to try and rob the place. Hopefully it was just some asshole who hadn't realized the bar was closing for the night. Or a customer forgot something. As quietly as he could, he crept out of the storage room, grabbing the bat that was usually kept close by and tiptoed to the front. 

Stiles peeked around the corner and saw one man sitting at the bar with his back to him. Stiles could only make out a head of jet black hair, broad shoulders, and a dark suit. Another man was behind the bar, scouring the several rows of bottles of alcohol. This man was tall, slender, also wearing a dark suit, and had curly, brunette hair. 

Stiles ducked back behind the wall, trying to calm his now racing heart. It didn't seem as if they were trying to rob the place since they weren't going for the cash register and they didn't seem dressed to commit a crime. Although, how one would dress to rob a bar, Stiles didn't know. 

Stiles took a steadying breath and stepped from behind the wall shielding him, the bat dangling loosely from his fingers. 

"Can I help you guys with something?" Stiles asked, his voice unwavering despite his heart damn near beating out of his chest. 

The curly haired man was already facing towards Stiles, having chosen a bottle off the shelf finally and was pouring the man at the bar a drink - who was now turning around to look at Stiles. 

Stiles' heart had basically stopped all together at this point. Once the dark haired man turned around to face Stiles he stood up, buttoning his jacket of his dark suit. He was tall - a couple of inches taller than Stiles even - and was dressed head to toe in a black, expensive looking suit, and there was something oddly familiar about him. The dark color of the suit accentuated his olive skin and green? Hazel? Jesus, what color would you even call that? Eyes. His face was completed with two thick, full eyebrows and dark stubble framing the frown on his face. The guy was freaking beautiful, okay? And Stiles never thought he'd refer to a man as "beautiful."

His accomplice was by no means ugly either. He was also wearing a black suit, but whereas the other gentleman had a more classically masculine yet beautiful face, the brunette was pale, his eyes were a clear blue, and his face cherubic in nature. 

The two men were watching Stiles, analyzing him, really, just as he had been, rather than answering his completely rhetorical question when another man walked out of where Finstock - Stiles' boss and the manager of the bar - office was. He was also dressed in a dark suit, was tall and broad shouldered, dark skinned with a shaved head, and also ridiculously attractive. Who were these people? A gang where the only requirements were owning a dark suit and being a male model?

"He's not here, boss, and I didn't-" 

The other man cut himself off when he saw Stiles, his hand going behind his back. Stiles didn't have to be a college graduate to know that he was reaching for a gun. Stiles really needed to start locking the doors when he was closing the bar. 

Before Stiles' fight or flight reflexes kicked in, the man who had been sitting at the bar looked at the dark skinned man and shook his head, causing the other man to relax, his hands going to his sides. 

"Who are you?" The dark haired man asked Stiles, starting to walk towards him. 

Stiles scoffed and tightened his grip on the bat, causing the man to stop. His eyebrow lifted as if to ask a question and Stiles could tell he was trying not to laugh. "I should be asking you that. In fact, I think I will. Who the hell are you guys? Follow up question: why the hell are you guys here?" 

"I'm Derek," the dark haired man, now identified as Derek said. He lifted his glass up, gesturing towards the curly haired man and the dark skin man, respectively. "This is Isaac and Boyd," he continued before taking a sip of his drink. Neither Isaac nor Boyd were showing any emotion on their faces, but they didn't take their eyes off of Stiles. 

Now that Stiles had been staring at Derek for so long and could put a name to his face, he could begin to place why he looked so familiar. Stiles had seen him in the local newspapers. 

And a few surveillance photos from his dad's case files. 

If Stiles' memory served him correctly, he was standing in front of Derek Hale, crime lord and mob boss of Beacon Hills. That title was an unofficial one, seeing as he was rumored to own all of California, and parts of Nevada and Oregon. Stiles' dad had worn himself ragged trying to find anything to charge the guy or anyone else in his "family" with. Over the last few years, Beacon Hills had been a goddamned war zone after the murder of Derek's parents by a rival mob boss by the name of Deucalion. After that, Derek's older sister, Laura was the head of the family, until she was murdered only a year and a half ago by Peter, their uncle, in an attempt to gain control of the family and as a peace offering to Deucalion. 

And then Peter and Deucalion were found dead only weeks apart. 

Derek was the number one suspect. 

This was all speculation, of course. None of the numerous charges and accusations thrown at Derek or his associates ever stuck. 

And now he was standing in the bar Stiles worked at with two equally sketchy dudes who were also probably in the mob. Great. 

"I'm looking for Bobby. You wouldn't know where to find him, would you?" Derek asked, completely oblivious to Stiles' revelation about his identity and internal freak out. 

Stiles sighed, running his fingers through his hair, making it stick up even more. Of course he was in this situation because of Finstock. The bastard was a walking bad luck charm. 

"I'm assuming he's at home. In his bed. Asleep. Like I wish I was right now," Stiles sassed. Let it be known that Stiles never claimed to have any sense of self preservation. 

To Derek's credit, he didn't attempt to strangle Stiles like he probably wanted to, but he did roll his eyes. "Bobby isn't at his house and he's not here," Derek said, now closing the distance between him and Stiles. "So where is he?" Derek continued. He was only a couple of inches taller than Stiles, but his presence was so intimidating Stiles expected him to be taller. 

Stiles looked Derek in the eye, defiantly almost. "I. Don't. Know. I'm not his keeper. Hell, the last time I saw him was a couple weeks ago when he gave me my check. Which was short, by the way. So if you find him, please tell that bastard he owes me the rest of my check." 

Stiles always had a problem with keeping his mouth shut, but at this particular moment he wished he had more practice in the art of shutting-the-hell-up. Being brutally murdered by a moss boss was a good way to go, he guessed. His funeral would definitely be closed casket though. 

Stiles mentally prepared to be swimming with the fishes, but nothing happened. Derek was watching Stiles, his eyes flickering all over his face, cataloguing every detail. Derek nodded, the corner of his mouth twitching like he wanted to smile. 

"Okay," Derek nodded. "Tell Bobby that I'm looking for him," Derek paused, his eyes lingering on Stiles' mouth before looking into his eyes again. "And that I'll be back."

Stiles felt an involuntary chill go down his spine. Whether it was from fear or arousal, he wasn't quite sure. 

He finally felt like he could breathe again when Derek stepped back to the bar and downed the rest of his drink in one go. He gestured to Isaac and Boyd, who had remained silent in throughout their exchange. 

Boyd walked out first, Isaac following him, and Derek bringing up the rear. Derek looked at Stiles one last time and smiled at him. A real, genuine smile, perfect teeth and everything. It was damn near blinding. His face completely transformed. He didn't look like a terrifying mob boss in that moment. He looked like a regular guy. 

Stiles was so screwed.


	2. the gallery

Finstock came into the bar only a few days after that terrifying and slightly arousing encounter with Derek and the others. Stiles relayed to him what happened and what Derek said, and as Stiles was talking, Finstock started losing color in his face and fidgeting. Stiles didn't even get the chance to yell at him about the missing money from his check before Finstock started swearing, then up and left again. 

The bastard. 

***

Finstock came back a couple hours later, looking a little more calm than when he left. He told Stiles he fixed everything and even gave him the missing money from his check. 

Stiles didn't think his heart could take any more surprises. 

And then, in walked Derek Hale. 

He was wearing a white dress shirt that was unbuttoned to reveal a patch of chest hair with the sleeves rolled up to his elbows, black dress pants, and black dress shoes. 

And he was alone this time. 

Stiles realized he was staring but so was just about everyone else in the bar. He quickly collected himself and went back to making the customer in front of him a margarita, even though he could see Derek walking towards the bar out of the corner of his eye. 

As if the first meeting with the gangster wasn't intimidating enough, now he was showing up during business hours and making the customers nervous. 

Stiles finished making the margarita and slid it across the bar to the man who ordered it. He looked like was going to sit at the bar but saw Derek walking towards him and scurried off. 

Coward. 

Derek sat down in the man's evacuated seat, looking just as ridiculously handsome as the last time Stiles saw him. 

"What can I get you?" Stiles asks. If his heart beat any harder he was sure it would beat right out of his chest. 

"I never got your name," Derek replied. "The other night, when I was in here," he clarified. "You know my name but I don't know yours," Derek smiled and leaned closer to Stiles. 

"Yeah, well, you didn't pay for that drink you had the other night either, so I'd say we're pretty much even." Stiles chewed on his bottom lip, once again cursing his big mouth. It's like he had a death wish or something. 

And again, Derek didn't kill him. 

Stiles took the chance for escape when a woman down at the end of the bar flagged him down for another drink.

Stiles filled the woman's drink order and could feel Derek's eyes on him the entire time. He sighed and rolled his eyes, walking back to where Derek was seated. 

"Are you going to order something? You're scaring the customers."

Derek chuckled softly. "I'll have a beer. Whatever's on tap is fine."

Stiles nodded and got a glass to fill his order. "My name's Stiles. Stilinski," he said deliberately, looking at Derek. "As in, Sheriff Stilinski. Also known as: my father."

If Derek cared about the knowledge that Stiles' dad was the Sheriff, he didn't seem surprised or outwardly upset. 

Stiles handed him his beer. 

"I'm guessing that's a nickname," Derek smirked, accepting his beer from Stiles and taking a sip. 

Stiles huffed out a laugh and nodded. "Yeah. My real name is Polish and unpronounceable. And no, I will not teach you how to say it. I don't care how good you are at pronouncing hard words or how many other languages you speak." 

Derek raised one of his thick eyebrows over the rim of the glass he was drinking from. "I'm assuming you hear that a lot?" Derek set his half full glass on the counter, wiping the foam from the beer off his mouth. 

Stiles watched him wipe the foam from his mouth with only barely contained lust. "If I had a nickel for every time I heard it..." Stiles shrugged. "You know the rest."

Stiles glanced at the door, more out of habit than anything else, and saw the only other bartender that worked at Triskele - Heather - walk in, which meant that Stiles' shift was over. 

"Can I top you off before I head out?" Stiles asked, his face heating up almost as soon as the words left his mouth. 

Derek raised one of his expressive eyebrows yet again. The corner of his mouth twitched, betraying that he was trying not to smile. "No, I'm good," he replied, standing up and pulling his wallet out of his back pocket. He pulled a few bills - way more than necessary for one beer. "This should take care of the whiskey from last time, the beer from this time," he paused and smiled this time. "And your tip."

Stiles took the money, mentally willing his face to remain expressionless, and put the right amount of money in the cash register and the rest in his pocket. 

He emptied out his tip jar and clocked out. 

And Derek was still standing there, like he was waiting for him or something. 

"You gonna walk me out or something?" Stiles scoffed and walked around the bar to where Derek was. 

Derek shrugged and put his hands in his pockets. "Yeah. That okay?"

Stiles' heart started working overtime. He swallowed, his mouth suddenly dry and shrugged, feigning nonchalance. "Yeah, sure," he mumbled. 

"Why were you looking for Finstock? And are you the reason why he suddenly gave me the missing money from my check?" Stiles questioned as they both walked out of the bar. 

Stiles' big mouth was also paired with a natural curiosity. They both got him in his fair share of trouble, but Derek had to be the most patient mobster in the world. 

Derek shrugged. "He owed me some money. And I may have persuaded Bobby to give you the money you were owed." He shrugged again. "No big deal."

Stiles chewed on his lip harder to keep the flow of questions racing through his mind at bay. 

They reached Stiles' jeep and Stiles turned to face Derek. "Well, this is me," Stiles stated the obvious. 

"Are you doing anything later?"

Stiles scoffed and stopped where he was unlocking his car door. "What, are you asking me out or something?" Stiles laughed, but then stopped at the serious look on Derek's face. 

"Are you fucking kidding me?" Stiles almost shouted. Again, with the big mouth. Derek looked surprised at Stiles' outburst, but didn't say anything. He just shrugged his shoulders again. "Okay, we only met a couple days ago, one," Stiles started, counting off with his fingers. "Two, you learned my name an hour ago. And three, my dad's the Sheriff and you're a criminal," Stiles enunciated. 

"Alleged criminal," Derek enunciated right back. "Nothing's ever been proven."

Stiles rolled his eyes again, opened his car door, got inside, and started the car. 

Derek tapped on the window, his usual calm façade slipping. He looked a little more human. Like the first time he smiled at Stiles. 

Stiles sighed and manually rolled down the window. It was an old Jeep, okay? 

"What?"

"Can I at least get your number?" Derek asked. He looked so hopeful, his eyes pleading. 

Stiles chewed on his bottom lip to keep from smiling. He didn't say anything for a few seconds, just watched Derek's eyes flicker from his to his mouth. After almost a full minute of silence, Stiles shook his head and buckled his seatbelt. "Watch your feet," Stiles warned before putting the car in gear and pulling out of the parking lot.

***

"I look like a waiter," Stiles sighed, fumbling with his tie. 

"You look fine," John, Stiles' dad, assured him. 

Stiles scoffed. "I'm pretty sure I wore these same clothes to that formal sophomore year that no one asked me to."

Stiles was wearing a red button down shirt, black jeans, and the cleanest pair of Vans he owned. His shirt was a size too small and the sleeves were too short, so Stiles had no choice but to roll them up. The pants were the only pair he had without holes or paint on them, but they were also his work pants so they still smelled faintly of beer, no matter how many times they were washed. 

"What are you all dressed up for, anyway?" John asked. 

Stiles gave up on his the tie and threw it on his bed. "There's an art show in the gallery downtown and a couple of my pantings are being featured," Stiles explained with barely contained excitement. "I thought I told you that?" Stiles grabbed his keys, wallet, phone, and walked out of his room, his dad following him down the stairs and into the kitchen. 

"I don't know, kid. Between your work hours and mine we barely see each other anymore."

Stiles was looking through the fridge, pulling out the lunch he'd prepared earlier and saved for his dad to take to work. Ever since his mom died when he was twelve, Stiles had been the one in charge of the meals, because if it were up to his dad they'd live off take out and Johnnie Walker whiskey.

"Yeah, I know. But the bills won't pay themselves," Stiles said as he balanced a couple of Tupperware containers on top of each other and shut the fridge with his foot. 

The Sheriff chuckled, "You shouldn't worry about that. I'm the parent, you're the kid," he said as he took the containers out of his son's hands. 

"Mhm," Stiles hummed noncommittally. They had this discussion just about every time they spoke and just usually agreed to disagree. "I made a variety this time so you'd have more options," Stiles changed the subject to the food he'd made. 

"Thanks," his dad mumbled. "I love eating rabbit food."

"Yeah, well, that rabbit food is saving your life. C'mon, we're both going to be late." 

***

They were late. 

The Jeep wasn't starting, for what was probably the millionth time, so Stiles called his mechanic who had it towed to his shop and Stiles' dad drove him to the gallery in his squad car. 

It was giving Stiles unfortunate flashbacks to freshman year of high school. 

By the time Stiles arrived at the gallery it was almost forty five minutes after it started. 

There were a decent amount of people there, all obviously richer and more educated than Stiles. 

At least there was alcohol. 

Stiles grabbed two glasses of champagne from a cater waiter's tray, chugged one of them, and set the empty glass back on his tray. The waiter didn't even bother to hide his contempt for Stiles. 

Stiles shrugged shipped his drink. "It's been a long day, alright," he mumbled, moving through the gallery and sipping on his champagne. 

"Stiles!"

Stiles turned around when he heard an annoyingly positive voice call his name. "Oh, hey Kira," he greeted the curator of the gallery. 

Kira contacted him a couple weeks ago through his Instagram. He didn't really use social media except to post his art. He thought it was a joke when she told him she was a curator for the gallery in Beacon Hills and wanted to feature a few of his paintings at the next art show. 

"You're late!" She scolded. "Where the hell have you been? People have been asking to meet you and I've had to stall." 

Kira was fuming. As much as Kira could fume. She was an Asian woman with shoulder-length, dark hair, she was shorter than Stiles by several inches. She was bubbly and positive, almost nauseatingly so. This was the first time Stiles had seen her even a little annoyed. Granted, he'd only known her for a couple weeks, but Stiles got the feeling that she wasn't easily angered. 

"I'm sorry, alright. I was already running late but then my Jeep died and it was a whole thing," Stiles ran his fingers through his hair, making his already messy hair stick up more.

"Well, you're here now, and that's all that matters," and just like that, Kira wasn't angry anymore. "Come on, there are still some people interested in meeting you."

Stiles groaned and drank the rest of his champagne. 

"It won't be that bad," Kira assured him as she looped their arms and dragged him to where he needed to be. 

***

Stiles spent the next hour listening to The Real Housewives of Beacon Hills critique his art work and haggle him over the price of his paintings. They were wearing two thousand dollar shoes but wanted to argue about lowering the price of an eighty dollar painting. He still managed to sell a couple of his paintings despite the complaining, though. 

There was still another hour of the show, but Stiles was hiding from Kira and the others. He was in the abstract art section sipping on his sixth glass of champagne, trying to figure out what the hell was going on in the painting on the wall. 

"I don't get it either."

"Holy shit!" Stiles jumped, his hand clutching his chest. "Derek! What the fuck, dude?"

Derek was standing next Stiles clearly trying not to laugh at him. "I thought you heard me walk up. I said 'hello'."

"Well, I'm a little drunk so my sense of awareness is all off," Stiles turned back to the painting on the wall. "Or the painting hypnotized me." He heard Derek chuckle and Stiles smiled a little. "What are you doing here? Are you following me or something?" Stiles was mostly kidding. It had been a little over a week since Derek came to the bar and asked Stiles out and he hadn't seen him since. 

Derek scoffed and rolled his eyes. "I'm not following you. I like art. And I own this place, so I like to drop in from time-to-time to make sure the building is still standing." 

Stiles downed the last of his champagne, set it on a passing waiter's tray, and sighed. "I'm either too drunk or not drunk enough to question the fact that a mobster owns an art gallery," Stiles said before turning and starting to walk away. 

"Where are you going?" Derek asked, following right behind him. 

Stiles shrugged. "Home? I don't think Kira will care if I skip out on the rest of the art show."

Derek grabbed Stiles' arm to stop him from walking. "You're drunk. I can give you a ride, if you want." 

"Isn't there an after school special about accepting rides from strange men," Stiles laughed. 

Derek rolled his eyes and let go of Stiles' arm. "Do you want a ride or not?"

Stiles giggled, holding his arms up in surrender. "I was just fucking with you. My Jeep's in the shop anyway and I don't trust ride sharing companies off principle alone."

Derek got that look on his face that said he was trying not to smile or laugh. "Come on," he said, leading Stiles out of the building and to his car, a black Camaro.

"Oh. My. God. Of course! Of course your car is expensive and attractive like you," Stiles exclaimed. The 'like you' part was supposed to be said in Stiles' head, but whatever. 

Derek smiled a little as he clicked the fob to unlock the doors. "Thanks. It was my sister's," He mumbled before getting into the driver's seat. 

Stiles slid into into the passenger's seat and buckled his seatbelt. Stiles was silent for a moment before speaking again as Derek pulled out of the parking lot. "What was she like?" If Derek bit his head off he could just blame it on the alcohol. 

Stiles saw the muscle in Derek's jaw jump like he was clenching it. But he answered, "A pain in the ass," Derek huffed out a laugh, shaking his head. "But she was...Good, y'know?" Derek swallowed, like he was swallowing down his emotions. "She was just really good." 

Derek's right hand was resting on the gear shift and Stiles didn't think about it before he grabbed Derek's, lacing their fingers together. 

Derek looked at Stiles, then their hands, then back to the road. But he didn't let go. 

"My mom died when I was a kid," Stiles blurted out, staring at their hands. "She had this rare form of dementia. Really aggressive, no cure," Stiles sighed, rubbing circles into the back of Derek's hand with his thumb. "She spent the last few months of her life in a hospital bed before dying." 

Derek squeezed Stiles' hand reassuringly and Stiles cleared his throat, getting ready to change the subject. "You said you own the gallery, right? Do you own any other places?"

"I own a couple of restaurants downtown, a club," Derek glanced at Stiles, smiling a little. "And the bar you work at." 

Stiles laughed. "Of course you do. What did Finstock owe you money for?" Once again, self preservation was not a virtue Stiles possessed. 

"I'm sure you can guess," Derek answered. 

He turned onto Stiles' street and pulled into his driveway. Derek let go of Stiles' hand to put the car in park and turn off the ignition before turning in his seat to face Stiles. 

"I want to hear you say it, though. And how the hell did you know where I live? I didn't even tell you."

Derek rolled his eyes. It was beginning to be their mutual way of communication. "Everyone knows you moved back here to help your dad after his heart attack and everyone also knows where the Sheriff lives. This town isn't that big, Stiles. And I'm not telling you what the money was for. The less you know, the better."

Stiles rolled his eyes right back at Derek and unbuckled his seat belt. "Fine, but don't act all surprised when I ask you about it again, because I will." He opened the door and was about to get out, but paused and looked back at Derek. "Aren't you gonna walk me to my door?" Stiles batted his eyelashes and tried to look innocent. 

Derek sighed and got out of the car at the same time as Stiles and walked side-by-side up the driveway. "I don't even know why I'm doing all this, after you rejected me," Derek teased, knocking his shoulder against Stiles'. 

Stiles didn't say anything until they got to his door, the fluorescent porch light the only way they can see each other clearly. "Ask me again," Stiles leaned back against his front door, looking into Derek's green/hazel with his honey-colored brown ones. 

"Ask you what?" Derek smirked. 

Stiles groaned, pushing off the door and closing some of the space between him and Derek. "Ask me out again." Stiles licked his lips, a nervous habit. 

Derek's eyes flicked down to Stiles' mouth, all traces of humor gone. "Will you go out with me?"

Stiles' smile grew with the passing moments and he nodded. "Sure, why not?" He said nonchalantly, despite his heart racing and his palms sweating. Stiles leaned in close to Derek and slipped his hand into his suit jacket pocket, finding his phone and pulling it out. 

"What are you doing?" Derek asked but made no move to stop Stiles. 

"I'm giving you my number," Stiles said as his thumbs flew over the keys of the phone. "There. I sent myself a text too, so I'd have your number," Stiles said as he slipped Derek's phone back into his jacket pocket. 

"Goodnight, Stiles," Derek said, and before Stiles knew it, they were kissing. It was a short kiss, chaste, like how someone would kiss a family member. But Stiles felt like his whole body was on fire none the less. He was still standing there, gently prodding his tingly lips with his fingers as Derek got into his car and started it. 

"Goodnight, Derek," Stiles mumbled to himself before snapping out of his daze and unlocking the front door. 

He closed the door behind himself and smacked the back of his head against it. 

"Fuck."

**Notes for the Chapter:**

> [follow my personal tumblr](http://cursed-kid.tumblr.com)   
>  [fandom tumblr](http://hecks-eyebrows.tumblr.com)   
>  [my beta's tumblr](http://sassyhunters.tumblr.com)


	3. questions & answers

**Notes for the Chapter:**

> It took me forever to finish this but here you go! Thanks for all the comments and kudos, I really appreciate it ❤️❤️❤️

Stiles groaned as rolled over on his side, away from the sun streaming in through his uncovered window. He must have forgotten to close his shades before he passed out last night. 

Stiles tried going back to sleep, but now that he was cognizant, the throbbing of his head was unbearable. 

Stiles made some more inhuman noises to voice his discomfort before throwing the covers off and stalking to the bathroom. He looked at himself in the mirror, against his better judgement, taking in the dark circles under his eyes and the fact that he was still in the clothes he wore to the gallery. 

Stiles shook his head to himself before carrying on with his morning routine. 

Once Stiles showered and brushed his teeth he dressed in his comfiest sweatpants and Beacon Hills High School Lacrosse hoodie. He almost felt like a real person again. 

He walked down the stairs and into the kitchen where his dad was already sitting at the table in his uniform, reading the newspaper and drinking coffee, even though it was well into the afternoon. 

Stiles still made a beeline for said coffee, grunting in acknowledgment to his father when he greeted him. 

"Rough night?" The Sheriff smirked.

Stiles sighed and nodded as he moved across the kitchen to get the Aspirin for his headache. He popped three pills into his mouth and washed it down with his coffee, the hot liquid burning his tongue and mouth. "It was," Stiles mumbled, taking his mug of coffee and sitting down across from his dad. 

The Sheriff chuckled softly. "I thought you were going to an art show?" 

He nodded again. "I was. I did. There was a lot of free champagne," Stiles shrugged, lifting his mug to his lips to take a sip before speaking again. "You know I love free stuff." 

The Sheriff rolled his eyes fondly at his son before looking at his paper again. 

"I thought you had the day off," Stiles narrowed his eyes at his father. 

John sighed, pretending to read to avoid Stiles' gaze. "A couple deputies called in sick so I've been picking up some of the slack," the Sheriff shrugged and took a sip of his coffee. 

Stiles frowned. "It's only been two months, dad. I know you've been doing better, but I don't want you to do too much too soon." Since John had been cleared to work again, Stiles and John both thought it was best for him gradually start back working the same hours he was pre-heart attack. But now John was trying to work another twelve hour shift after _only_ working twelve hour shifts for the last few days. He needed a break. "Plus, I thought we were gonna do something today. That's why I made sure I wasn't scheduled to work. We barely see each other," Stiles mumbled, staring into his coffee. 

Stiles and his dad had a rocky relationship following the death of his mother, Claudia. John threw himself into work and alcohol to deal with the grief of losing his wife but ultimately left his son to fend for himself. Stiles didn't have any support after his mom passed which caused him to act out and rebel.

Stiles' Rebellious Phase caused a huge rift between Stiles and his dad. Stiles was lying, sneaking out, partying. It took John almost losing his job, Stiles getting arrested, and a lot of therapy for them to even _begin_ to repair their relationship. 

John nodded as he got up to dump the rest of his coffee in the sink. "I know, but we're short staffed, so there's nothing I can do." John rinsed his mug out before setting it in the sink and turning back around to face his son. "But, I think we're gonna get a little more help soon." Stiles grunted to let his dad know he was listening. "Someone from the FBI field office in Los Angeles has been in contact with me about starting some sort of organized crime task force." 

Stiles choked on the coffee he had been drinking. 

"The FBI? Really, dad? How would that even work?" Stiles laughed nervously. 

"Well, they'd send a couple of their agents down here. They'd need a couple of my guys to help complete the task force, but I think it'll help in the long run. Some of the deputies will be investigating the regular crimes and the other deputies will be investigating the crimes connected to Hale and his crew," John stated. 

"But I thought things were winding down now? Why the need for a task force?" Stiles questioned. 

"Yeah, but Hale and the rest of them are still out there," the Sheriff shook his head, visibly disgusted. "You weren't here when all those people were dying. Everyday, a new body or someone going missing," John scoffed in disbelief, shaking his head again. "Anyway, I've got to get to work." John grabbed his keys off the table and ruffled Stiles' hair as he walked past him. "I'll see you later." 

Stiles grunted in acknowledgment, already going over in his mind what his dad told him. He didn't know what to do with this new information. Stiles knew in theory that Derek had killed people, but now his dad was basically confirming it and making him sound like a cold-blooded psychopath. He just couldn't reconcile the Derek he knew with the man his dad was describing. 

But that was it, wasn't it? Stiles didn't _know_ Derek at all. 

Stiles got up and dumped his coffee in the sink and went upstairs to his room, checking his phone for the first time since last night. He had a couple texts from his mechanic about his Jeep. The engine and car battery, along with a few other mild problems were affecting his car's ability to perform. Stiles let out a long groan when he read how much his mechanic was charging him. It was going to cost him almost a thousand dollars. He had some money saved up for when the Jeep inevitably broke down but it was nowhere near the amount he needed. 

Stiles flopped onto his bed and replied to his mechanic that he'd get the money, he just needed a few days. It'd probably be easier to just get a new car, but Stiles' Jeep had a special place in his heart because it used to be his mom's. It was the only thing he had left of her besides a few pictures. 

He kept scrolling through his notifications until he came up on a text from Derek. It was sent in the morning, when Stiles was still asleep. 

**Derek 9:08am**  
_How are you feeling? ___

____

Stiles chewed on his bottom lip, fighting the smile that was threatening to form. Stiles shouldn't be so excited to hear from Derek, especially after the conversation that just took place with his dad. 

But then Stiles thinks about the moments when he's with Derek and the stoic mask he keeps up disappears. Derek will smile or chuckle or roll his eyes and Stiles knows he's seeing a glimpse of the real Derek. 

Stiles reads the text again and internally debates himself for a few seconds more before rolling his eyes and mumbling, "Fuck it." 

Stiles pressed the phone icon below Derek's name to call him. He got off his bed and paced the length of the room as the phone rang twice before stopping when Derek picked up with a gruff, "Hello?" 

"Uh, hey. It's me. Stiles. I just woke up so I just saw your text. Well, not _just_ woke up. I woke up a reasonable amount of time ago but I only just now saw your text and wanted to tell you 'I'm fine'. Which I am also now realizing I could have just text you instead of interrupting-" Stiles was gearing up for one of his epic rambles when Derek thankfully cut him off. 

"Stiles, it's fine," Derek assured him. "You can call me whenever you like." 

Stiles stopped pacing and sat in his computer chair. "Yeah?" Stiles grinned. "Well, I just wanted to let you know I was okay. A little hungover still, but that's to be expected." 

"Anything I can do?" Derek asked. 

"I'd love something greasy to eat. That's my go-to hangover cure," Stiles said as he leaned back in his chair. 

Derek was silent for a few seconds before speaking again, his voice, soft, almost shy. "We could get something to eat, if you want?" 

Stiles sat up again at Derek's question, his mouth opening and closing a couple of times before he answered. "Um, yeah, sure. I mean, I can't meet you anywhere or anything because my Jeep's still in the shop. But you could come here? Like, to my house, where I live." Stiles face-palmed at his own stupidity. "What I mean is," Stiles exhaled a breath and leaned back again to stare up at his ceiling. "My dad's not home, so you could come over and...Hang out," Stiles cringed at how awkward he was and waited for Derek to respond. 

"Yeah, that's sounds great," Derek agreed. Stiles spun around in his chair and fist pumped in victory. 

"Cool," Stiles feigned nonchalance. "There's this diner a couple blocks from the bar that makes the best burgers and curly fries. All the cholesterol and sodium needed to stop a heart." 

Derek chuckled. "I know the place. I have to finish up a couple of things first, but I'll be over in about an hour. That okay?" 

Stiles wanted to ask what he had to finish up but held his tongue for the time being. "Yeah, that's fine." 

They said their goodbyes and after Stiles hung up he did another spin in his computer chair to celebrate. 

Stiles turned on his laptop and decided to check his social media accounts and email while he waited. He responded to a couple inquiries on Etsy and one from Kira about another upcoming art show. 

Stiles was scrolling through his Instagram feed when he heard a car door open and shut. He closed his laptop and ran his fingers through his hair. Stiles looked down at the old hoodie and sweatpants he was wearing and found himself wishing he had the foresight to look more presentable. 

The doorbell rang and Stiles shook himself from his thoughts and got up to answer the door. It wasn't like this was a date. There was no reason for Stiles to dress up. They were just two guys hanging out at one guy's house. And if they so happened to have a mutual interest in each other, that was just a coincidence. It _wasn't_ a date. Stiles descended the stairs quickly, giving a cursory look around the living room to make sure nothing embarrassing was left out and opened the door. 

It took Stiles' brain a moment to catch up to what his eyes were seeing. Derek wasn't wearing his usual suit. He was in dark wash, tight jeans, a blue crew neck t-shirt, and a leather jacket. He looked like he stepped right out of GQ magazine. 

"Are you gonna let me in?" Derek smirked like he could tell exactly what Stiles was thinking. Stiles picked his jaw up off the floor and moved out of the way. 

"You're not wearing a suit," Stiles stated the obvious, closing the door behind them after Derek walked in. 

Derek was looking around the living room holding a plastic bag of their food in one hand and a drink carrier with two cups in the other. He turned back around to face Stiles, still smirking, his eyebrow raised but he didn't say anything. Stiles took that as a nonverbal question. 

"I've only seen you in suits or part of a suit or something," Stiles clarified. 

Derek shrugged and answered, "Today was my day off." 

Stiles had about five more questions enter his mind when he said that, but Derek spoke again before Stiles could ask. 

"Where should I put this?" Derek asked, nodding to the food and drinks in his hands. 

"We could eat in the dining room?" Stiles suggested, leading them to the room. 

Derek set the food and drinks down on the table and started distributing it. "I wasn't sure what kind of burger you wanted so I just got the double bacon cheeseburger with curly fries. Is that alright?" Derek asked. 

Stiles could cry that's how perfect it sounded. His stomach must have agreed because it chose that moment to rumble loudly. Stiles laughed, his face heating up in embarrassment. "Yeah, that's what I usually get anyway," Stiles said, taking his food and sitting down. Derek smiled a little and set a drink down in front of Stiles. He took off his leather jacket exposing his biceps and hairy forearms and draped the jacket over his chair. Derek sat down across from Stiles, his knee gently knocking the other man's. 

Stiles felt his face heating up again at just that small amount of contact. He compensated by taking a huge bite of his burger, moaning at the taste. The only thing he had all day was aspirin and coffee, so he was good and hungry. Stiles continued to stuff his face, licking his fingers and moaning occasionally to express how good his food was. He spared a glance at Derek, who looked like he was either trying not to laugh or constipated. Maybe both. Stiles chewed and swallowed the food in his mouth before speaking (he did have _some_ manners), "What?" 

Derek laughed softly and shook his head. "Nothing. I've just never seen someone eat so enthusiastically before." 

Stiles scoffed before taking a long sip of his drink. "Well, you're obviously hanging around the wrong people," He said before shoveling some fries into his mouth. 

"Obviously," Derek agreed. 

They ate in companionable silence after that. It wasn't awkward and Stiles surprisingly didn't feel the need to fill the silence with the sound of his voice. They exchanged flirty smiles and prolonged eye contact. Derek even let Stiles rest his leg against his. It was feeling very... Date-like. 

"Is this a date?" Stiles suddenly blurted out. 

Derek lifted one of his eyebrows. "Do you want this to be a date?" Derek turned the question back in Stiles. 

"No! I mean, yes! I mean-" Stiles groaned and ate the remainder of his fries, using the time he spent chewing to actually think about what he was trying to say. "I think I want to date you," Stiles finally said once he swallowed his food. 

"You think?" Derek questioned, his other eyebrow going the first one. 

"Yeah," Stiles nodded. "But I want to know what I'm getting myself into." 

"Meaning?" 

Stiles rolled his eyes. "Don't play dumb, okay? If we're going to keep... Hanging out, then we should get to know each other better. I should get to know you better. Criminal stuff included." Stiles collected his garbage and stood up, throwing it in the trash. He didn't think his request was unreasonable. If Derek was a regular guy with a regular job that he was kind-of-sort-of dating, then he'd want to know the same things. Stiles heard Derek's chair scrape across the floor as he stood up and walked to where he was by the trash can. Derek threw his trash in the bin as well and stood in front of Stiles with his arms crossed. 

"And how do I know you're not going to run off and tell your dad everything I say. You're the one who keeps mentioning that your dad's the Sheriff." 

"Okay, you have a point there. But, if I was going to tell my dad anything I would have told him that you were at the bar, _twice_ and that you asked me out. I could have told him that you were at the gallery. And I could even call him right now and tell him you're at the house. But I haven't done any of that and I won't. So stop making excuses and either tell me or don't." Stiles crossed his arms right back at Derek. They were now in a staring match, waiting for someone to crack. 

It couldn't have been more than a minute that went by before Derek was rolling his eyes and uncrossing his arms. "Fine." 

Stiles smiled at having gotten his way. He had a feeling that would happen a lot. "Come on." He grabbed Derek's hand and led him into the living room and sat down on the couch, pulling Derek down next to him. Stiles didn't let go of Derek's hand once they sat down. Instead, he laced their fingers together like last night. "The FBI is coming here," Stiles blurted out. 

Both of Derek's eyebrows lifted this time. They basically had their own language. "How do you know that?" Derek asked. 

"My dad told me. Said they were sending a couple agents here to help investigate you." Derek's face remained unchanged, like he could care less. "Aren't you gonna freak out or something?" Stiles asked. 

"I can handle the Feds. They're not going to find anything." 

"Your confidence is such a turn on," Stiles said sarcastically. Derek smirked and Stiles felt his face heat up. 

"Why did you tell me that?" Derek asked, thankfully steering the conversation back. 

Stiles shrugged. "I told you something now you have to tell me something," Stiles paused, "Well, _some things_ , plural." 

Derek looked like he was already regretting agreeing to this. "Ask away." 

Stiles thought for a moment, his face becoming serious as he organized his thoughts. "What did you mean when you said "today was your day off"? Crime takes days off? And you never told me why my boss owes you money. How do you own the bar and all those other businesses you named? Have you killed people?" Stiles was starting to ramble, but quickly shut his mouth after the last question tumbled out. He meant to ease into the murder question, but Stiles had no tact. 

Derek sighed but didn't seem upset or angry by Stiles' questions. "Are you sure you want to know the answers to some of these?" 

Stiles nodded. "I told you; I want to know everything about you. Even the bad stuff," Stiles reiterated. 

Derek sighed again and looked down at their clasped hands. "I own Hale Construction. Y'know, that huge building building downtown with my name on it? It's obviously a front but I still have to show my face there from time-to-time and pretend like it's a normal business. Finstock owes me money because he loves to gamble. That's how I got the bar and some of the other places I own, but not all of them. Some are legitimate." He paused before answering the last question, rubbing his thumb over Stiles' knuckles. Derek had been staring at their joined hands the whole time he was speaking, but now he was looking Stiles in the eyes. "I have killed people. But only the ones who deserved it." 

This was one of the rare times Stiles was speechless. He had about a million more questions circling his head, but Stiles was really stuck on the whole "murder" thing. 

"I can't change who I am or what I've done. I'm telling you right now that I'm not a good guy, Stiles," Derek spoke seriously, his green eyes boring holes into Stiles' brown ones. "So, if you don't want to see me again, I'd understand." 

"You're not getting rid of me that easy, dude," Stiles scoffed. 

Derek rolled his eyes but Stiles could see that he was trying not to smile. "Aren't you the one who called me a 'dangerous criminal' the first time I asked you out?" Derek teased, slowly moving closer to Stiles. 

Stiles leaned back against the arm of the couch as Derek crawled on top of him. It reminded him of watching the Discovery channel and seeing a predator stalk its prey. 

Stiles' heart was thumping hard in his chest, more from anticipation than anything else. Stiles licked his lips as Derek hovered above him, caging him in with his hands by Stiles' head. "I think I just said the 'criminal' part," Stiles teased. "You must have subconsciously added the 'dangerous' part," Stiles bit his bottom lip, watching as Derek's eyes flickered from his mouth to his eyes. 

Stiles wrapped his legs around Derek's thighs, pulling them closer so that Derek's body was almost completely enveloping Stiles'. "You gonna kiss me or what?" Stiles goaded him. 

Derek smiled wide - perfect teeth, dimples, and all. "So bossy," he mumbled before pressing his lips to Stiles'. 

Derek's lips were soft, a contrast to his rough stubble. He kissed Stiles slowly, almost hesitantly, like he was afraid that Stiles would push him away. 

Stiles deepened the kiss, his hands tracing Derek's stubbled jaw before tangling them in his dark hair. Derek's tongue darted out and flicked over Stiles' lips, asking for entrance. Their tongues met, the kiss quickly turning heated, Stiles' hands moving down Derek's back, and up his chest, before finally resting on his waist. 

Derek pulled away first, kissing Stiles' moles on the side of his face and down his neck. He laughed softly, Derek's stubble tickling his neck. "Derek? You should go," Stiles said, running his fingers through the other man's hair. Derek looked up from where he working on a hickey on the underside of Stiles' jaw. 

"Why? What's wrong?" 

Stiles shook his head and sighed. "I really want you to stay, but my dad's shift ends at like, the ass-crack of dawn. And I haven't snuck someone out of my room since high school and I intend to keep it that way." 

Derek huffed in annoyance but agreed. "Okay," he mumbled, bending down and pecking Stiles on the lips once before crawling off of him. 

Stiles got up as well, the both of them ignoring the obvious erections in each other's pants as they walked the twenty feet to the front door. 

Derek turned back around to face Stiles once they reached the door, wrapping his arms around his waist. "You can text or call me whenever you want. I'll answer," Derek said, cupping Stiles' cheek and kissing him again. 

Stiles let him be the one to pull away first again, but kept Derek close by hooking his fingers in the his belt loops. "And I'm sure you'll be coming by the bar," Stiles teased, stepping back from him. 

Derek smiled and opened the door. "Bye, Stiles," he said before walking outside to his car. 

"Bye, Derek," Stiles mumbled to himself, watching as Derek got in his car and drove away. 

**Notes for the Chapter:**

> [follow my personal tumblr](http://cursed-kid.tumblr.com)   
>  [fandom tumblr](http://hecks-eyebrows.tumblr.com)   
>  [my beta's tumblr](http://sassyhunters.tumblr.com)


	4. the date

**Notes for the Chapter:**

> I know it's been awhile since I last updated, please don't kill me. I love all your nice comments and kudos, please keep them coming!! Notice the rating change from Teen to Explicit, I attempted to write smut for the first time

"I'll probably be back late, so don't wait up," Stiles said to his dad, walking past him in the living room to the front door. He was hoping that he could make it out the door without an interrogation, but Stiles has never been that lucky.

"Wait a minute, Stiles," John told his son. Stiles cursed to himself, his hand wrapped around the door, keys in hand. He turned around when he heard his dad get up and walk towards him. "Where are you going all dressed up?" 

"Um..." Stiles looked down at his outfit. He was wearing khaki pants, a navy blue Henley, and the cleanest pair of Converse he owned. It wasn't a suit, but it was the nicest thing Stiles has worn in weeks.

John didn't give him time to even think of a lie before he was speaking again. "You've been coming and going at all hours for the past month." Stiles opened his mouth to say something, but John spoke over him. "I know, you said you've been working more hours," John crossed his arms, looking at his son suspiciously. "But I think I know what's been going on." 

"Uh," Stiles chuckled nervously. "You do?"

"You're seeing Parrish again, aren't you?" The Sheriff guessed, looking smug.

Stiles sighed in both relief and exasperation before rolling his eyes. "No, Dad. I am not seeing Parrish again."

Jordan Parrish was Stiles' on again/off again boyfriend and John's favorite Beacon Hills deputy. Jordan and Stiles became close the summer before Stiles left for college and maintained a relationship off and on for the last four years Stiles was away. Once Stiles came back to Beacon Hills, Jordan was adamant about being in a serious relationship.

Stiles declined.

He didn't know who was more heart broken: Parrish or his dad.

John visibly deflated. "Well, you are seeing someone," He stated.

Stiles sighed again. He knew it was no use denying it when his dad knew something was up. "Yes, I am seeing someone," Stiles hurried to speak over John when it looked like he was going to interrupt him, "But it's still very new and we haven't even defined the relationship yet, so," He shrugged. At least that was the truth. For the past month Stiles and Derek have been spending more time together than not. And given all the time they've been spending together Stiles would say they're boyfriends, but past experiences have him wanting verbal confirmation.

Which Stiles intended to get if his dad would let him leave.

"Dad, can we finish this interrogation some other time?" Stiles whined. "You're making me late."

The Sheriff threw his hands up in defeat. "Fine. But I expect to meet whoever this guy is if you two get serious."

Yeah, like that was ever going to happen. But Stiles agreed anyway. "Noted," Stiles said and hurried out the door to his newly repaired Jeep, driving off before his dad could ask anymore questions.

Stiles and Derek spent the past month since their meeting getting to know one another. Stiles would invite Derek to the house when he knew his dad was working. Sometimes he'd cook for Derek and they'd talk and fool around on the couch for awhile before he went home. On the days when Stiles was too tired to cook, Derek would bring something for them to eat and they'd sit on the couch and watch a movie. After they ate they usually ended up swapping handjobs or blowjobs as the end credits of the movie played. Derek came by the bar more often, usually when Stiles was closing, but if he had the time he'd come into the bar in the middle of Stiles' shift to flirt with him and make the customers nervous before leaving again. 

And on the nights when they couldn't see each other, Stiles always called Derek before he went to bed and Derek always answered. 

Stiles tended to dominate most of their phone conversations seeing as Derek hated talking on the phone in any capacity. Stiles always started the conversation by asking how the older man's day went and Derek would answer with a general recap of his day that was probably only technically true. And then it was Stiles' turn to answer and that usually turned into a thirty minute rant about Finstock's incompetence, drunk assholes, and his desire to quit his job. Derek was always silently listening, adding in the occasional hum of agreement or grunt of acknowledgement when needed. Stiles called him out once during a rant about Ben Affleck as Batman, convinced he wasn't listening, and asked Derek to repeat what he said. 

He did. Almost word for word. 

It wasn't always Stiles complaining about working at Triskele or questionable casting choices. When there were lulls in the conversation Stiles would start up a game of 20 questions, trying to learn as much about the mob boss as possible. Derek was surprisingly open to answer any questions Stiles had as long as they weren't about his work (He wouldn't answer incriminating questions on the phone, only in person). 

Derek was the one to suggest they go out on a "real" date. Stiles had been under the impression that them just hanging out were dates - and Derek agreed - but was adamant about wanting to wine and dine him. 

And who was Stiles to deny him that? 

Stiles pulled into the parking lot of Gévaudan, the restaurant Derek chose, almost twenty minutes late. He parked next to Derek's Camaro, his blue Jeep out of place amongst the dark colored luxury vehicles, and walked quickly into the building. 

"Uh hi," Stiles greeted the hostess. 

She looked up from her phone, a look of contempt crossing her face, "We're not hiring right now," she said dismissively and looked back to her phone. 

Stiles scoffed. He knew he looked out of place amongst the designer clothes and diamonds but she didn't have to be rude. "Actually, I'm meeting someone here and they have a reservation. It should be under Hale. _Derek_ Hale." 

The hostess visibly paled at the mention of Derek and scrambled to get him a menu. "Oh! I am so sorry," she laughed nervously, her face burning red. "Right this way." Stiles followed behind her, fighting a smile the whole way to Derek's table. 

Derek was seated at a one of the tables near the back of the restaurant. He was seated facing them, his brows furrowed in concentration as he looked at something on his phone. 

Derek looked up at them when they were a few feet away, his lips quirking up in a small smile. He stood up once they reached the table, the hostess setting Stiles' menu down and leaving just as fast as she came, muttering about the waiter being with them shortly, her face still red.

Derek watched her hasty retreat, one of his eyebrows raised at Stiles. 

"It was nothing," Stiles dismisses, wrapping his arms around his date's neck. "She was just kind of a dick to me before she found out who I was with," he continued, then pressed a chaste kiss to Derek's lips and started to move away to sit down. Derek's arms were around Stiles' waist and they tightened around him so he wouldn't move away yet. 

"What did she say?" Derek asked, head tipped to the side. 

Stiles rolled his eyes, brushed Derek's arms off of him and sat down at the table, Derek following suit. "People are staring," he stated, eyes flicking over to some of the wealthy patrons in the room who were trying not to look at them and failing. In the rare occasions Stiles and Derek were seen out together people tended to stare. When it was just Stiles running to the supermarket or pumping gas, people tended to give him a wide berth or the occasional side eye. "Besides, it wasn't important and I'm sure she's already upset." 

Derek was frowning as looked down at the menu and changed the subject. He knew by now that Stiles was as stubborn as he was. "Why were you late?" Derek asked. "I was getting a little worried," he mumbled. Derek expressing any kind of emotion or feeling was few and far between. If he felt the need to say it in the first place he must have been more just "a little" worried. 

Stiles pressed his leg to Derek's. "I know, I'm sorry. I was already running late because of work and my dad was home so he decided to interrogate me." Derek's response was cut off by the waiter greeting them and pouring them both a glass of wine. It was Stiles' turn to raise an eyebrow at him. 

"What did your dad say?" Derek asked after telling the waiter to give them a few minutes to look over the menu. Derek had made it clear he didn't care if Stiles' dad - aka the Sheriff, aka the man who wants Derek's head on a platter - knew about them or not. 

"He knows I'm dating someone but he didn't press. I don't think he knows it's you," Stiles answered. The less his dad knew the better. 

"Did you already order that before I got here?" Stiles pointed at their wine glasses. 

Derek shrugged. "When I got here I told them I was waiting for someone. I always get this wine when I come here," the older man said as he continued looking through the menu.

Stiles hummed, flipping the menu as well. "Derek," Stiles said gravely after a few seconds of silence, eyes skimming the menu. "One appetizer is $20. A burger is $40. I'm not even going to look at the steak." 

Derek reached across the table, grabbing Stiles' hand to stop him before he could really get going. "Stiles, it's fine. I'm paying for everything, so get whatever you want." 

Stiles narrowed his eyes at Derek, causing the other man to sigh. He was gearing up for an argument. "You know I hate when you pay for me." They'd already had this argument when Derek took it upon himself to pay for the repairs on the Jeep. He was flattered that Derek did that for him but Stiles was a proud, independent person and he didn't want to feel like a charity case. 

"I asked you out so that means I pay," Derek reasoned. 

Stiles' eyes stayed narrowed as he thought. After another couple seconds of silence, he spoke. "I'm only agreeing with you because I'm hungry but any other time this would be an argument," Stiles said before looking back at the menu. 

Derek chuckled at Stiles' quick acquiescence. "Noted." 

Once the waiter came back around to take their orders (Derek ordered a steak with a Caesar's salad and Stiles ordered the surf and turf, one of the more expensive things on the menu), the two men fell into their usual routines of talking about their day, Stiles getting off-topic more times than not. When the food arrived they ate in companionable silence, Stiles' ankle hooked around Derek's. 

***

Derek paid for dinner with minimal complaints from Stiles but conceded when he offered to leave the tip. They joined hands on the way out, both of them pointedly ignoring the looks of the other patrons. 

"Well, this is me," Stiles said as they came to a stop beside his Jeep. Derek pressed him back against the car, his hands on Stiles' waist, face buried in his neck. Stiles wrapped his arms around Derek's neck, laughing when the other man's stubble tickled him. 

"Do you want to come back to my place?" Derek mumbled in between pressing kisses to Stiles' neck. 

Stiles leaned back, gently pushing Derek back with a hand on his chest so he could look at him. "Your place? As in, your house? Like, where you live?"

Derek huffed a laugh. "Yes, Stiles." 

Stiles couldn't help the grin that broke across his face. Any time they hung out it was always at Stiles' house or the bar. He hadn’t questioned it before because he knew it would be a huge step for Derek. The fact that Derek was inviting him now had to mean that he trusted him. 

"I’ll follow you?" Stiles suggested. 

"Okay," Derek agreed. He brushed his lips against Stiles' in a soft kiss then pulled away to get into his car, Stiles doing the same. He sent a quick text to his dad telling him he wouldn't be home tonight as Derek pulled out of the parking lot, Stiles putting the Jeep in gear and following behind him. 

***

"This place is fucking insane!" Stiles exclaimed. He was standing on the balcony in Derek's room looking out at the pool and the woods beyond. 

It took nearly twenty minutes for them to drive to Derek's place on the outskirts of Beacon Hills. The estate was surrounded by an eight foot, wrought iron gate that could only be accessed with the security code, there were several armed guards patrolling the area, and security cameras. The place was a goddamn fortress. 

Derek gave him a brief tour of the house before Stiles insisted he see Derek's room. Stiles didn't have to look in any of the other bedrooms to know his was the biggest. A king sized bed took up the right side of the room. There was a nightstand on one side of the bed with a book and reading glasses laying on top of it. Aside from the ridiculous balcony and great view, the room had a connecting bathroom with a large shower and a whirlpool tub. 

Stiles walked off the balcony and back into the room, sliding the glass doors closed behind him and drawing the shades closed. 

"You don't live here by yourself, do you?" Stiles called out to Derek who was in his walk-in closet. 

Stiles walked over to his dresser where there were two framed pictures on top of it, the only personal touches in the room. He picked up one picture frame that had a man and woman in a tuxedo and wedding dress respectively. It didn't take long for Stiles to come to the conclusion that they were Derek's parents. He gently set the picture back down and picked up the other one, a family photo that was several years old. It was taken at the beach, Derek's parents crouching down in the sand with a young Derek, Laura, and their other sister, Cora. They were all soaking wet and smiling wide like the picture was taken while they were laughing. 

"Members of my family all have rooms here, but I'm the only one that lives here the whole time," Derek answered, walking out of the closet and standing behind Stiles. 

"How old were you in this?" Stiles asked, turning his head to look at Derek. He had taken off his suit jacket, left a few buttons undone on his button down, and took off his cuff links. He was barefoot too, as was Stiles, his footsteps quiet on the lush carpet. 

Derek took the picture out of Stiles' hands, his lip quirking up at the edges in an aborted smile. "Maybe seven. Laura would have been ten and Cora was five. I remember this day so well. For some reason Cora really wanted to go to the beach even though it was the middle of November," he chuckled, remembering. "But she was the baby so she got whatever she wanted, especially when it came to my dad. So we packed up the car and went to the beach. The water was so cold and we had to keep running out to get warm," Derek smiled a little at memory and put the frame back where it belonged. 

Derek didn’t share information about his deceased family or childhood often. He usually said something in passing about his mom but then quickly change the subject like he didn’t want to talk about it. Stiles counted this time as a win and was dying to ask more about his family but he could tell by Derek’s body language that now wasn’t the time. 

"So why did you invite me back here?" Stiles turned around fully to face Derek. His face barely changed but Stiles could tell he was thankful for the change in subject. "You've never asked me to your house before." 

"I trust you," Derek shrugged. He didn't express his thoughts or feelings, often preferring to show rather than tell. But it was still nice to be validated. 

Which reminded Stiles: "We're exclusive, right?" One of Derek's expressive eyebrows lifted, causing Stiles to word vomit before Derek could get a word in edgewise. "I mean, we've been hanging out a lot so that would lead any rational person to think we're together. “Together” as in, we're boyfriends. Or partners. Not like, business partners, but partners in the romantic sense. Either way, I'm not seeing anyone else and I'd appreciate it if you didn't either," Stiles said, ending his rant with a defiant crossing of his arms. 

Derek's other eyebrow joined his first one. "Are you done?" He asked, trying not to smile. 

Stiles narrowed his eyes at the other man but nodded once. 

Derek pulled Stiles closer to him by his belt loops, his eyes dark and intense in the dim lighting of the room. Stiles could feel his neck and face heating up at the other man’s serious expression. 

“We are exclusive. I’m not seeing anyone else. And I’m a little old to be someone’s boyfriend, but if you want to call me that, that’s fine,” Derek spoke emphatically. “Okay?” 

Stiles’ smile was wide and smug. “Everyone in this whole town thinks you’re so tough and scary and mean, but I know the truth, Derek Hale,” Stiles teased, tugging on his shirt. “You’re just a big ole softie and-“ 

Stiles was cut off when Derek sighed and kissed him. Stiles was stunned for a moment before his brain kicked back online and he returned the kiss, his lips moving against Derek’s slowly. Stiles wound his arms around Derek’s neck, deepening the kiss as Derek wrapped his arms around his waist. 

Stiles twisted his fingers into Derek’s dark hair and tugged gently, eliciting a quiet groan from the older man. Derek brought his hands down from Stiles’ waist to roughly cup his ass, letting their clothed erections rub together in the process. Stiles moaned into the kiss, breaking it. Derek kissed each mole on Stiles’ cheek, following the pattern of moles down down his neck. 

“Bed. Now,” Stiles panted. 

Derek grunted in agreement and stopped working on the hickey he was sucking into Stiles’ skin and lifted him up, carrying him over to the bed and laying him down. 

“Show off,” Stiles mumbled, completely pretending like that wasn’t one of the hottest things he’d ever experienced. 

Derek smirked, calling his bluff. “You loved it,” he said, quickly unbuttoning his shirt and removing it. 

Stiles couldn’t even argue with Derek, too busy being distracted by his sculpted and hirsute chest and abs. 

They stripped each other quickly, clothes flying haphazardly, their kisses heated. 

“How do you want me?” Stiles panted. They both had a thin sheen of sweat on them from kissing and groping each other. Derek was rummaging through his nightstand looking for the lube and a condom. 

“Just like that,” Derek answered once he found what he was looking for. He took one of the many extra pillows on the bed and tapped Stiles on the hip, gesturing for him to get his hips up. Derek put the pillow underneath him so his hips were propped up and he would be more comfortable. He slicked his fingers with the lube and kissed Stiles passionately as he fingered him open. 

“Okay, I’m ready. You need to fuck me, like, now,” Stiles demanded three fingers later when he felt like he’d been prepped enough, groaning softly when Derek pulled his fingers out. He patted the bed blindly until his hand felt the foil of the condom and ripped it open. 

Stiles rolled the condom onto Derek and he slicked himself up with more lube before pressing the tip of his dick to Stiles’ hole and slowly pushing in. 

It had been a while for Stiles so it was a little painful as Derek bottomed out. He stayed still, giving Stiles time to adjust and relax, kissing him all over his face and down his neck before Stiles told him to move. Derek pulled out slowly, almost all the way, then bottomed out again. He repeated this a few more times, slowly pulling out and then quickly filling Stiles up. 

“Faster,” Stiles gasped, wrapping his legs around Derek’s waist. 

Derek did as told and moved faster, the room loud with the sounds of their fucking. He buried his face in Stiles’ neck, panting open mouthed against his throat as he rocked into him hard and fast. 

Stiles’ hands were all over the place: in Derek’s hair, gripping his back, his shoulders, before finding there home holding onto his ass. 

“Oh my god - uh, you’re so - ah, hot,” Stiles groaned. Even during sex he had to talk. “I’m so fucking close, Der,” he gasped out, his hands back in Derek’s hair. 

Derek leaned up, pressing his and Stiles’ foreheads together as he slammed into him. Both their eyes were wide open, their mouths open, panting and licking into each other’s mouths. Stiles snaked a hand in between the two of their sweaty bodies and wrapped a hand around himself, jerking himself in time with Derek’s thrusts as he looked him in the eyes. 

“Come for me,” Derek whispered. 

That, coupled with keeping his eyes on Derek and a few well-timed thrusts led Stiles to feel that familiar heat pooling in his groin, the only warning he had before he came all over himself and Derek. 

Derek moaned quietly when Stiles came, his hips jerking erratically several times before filling the condom. He laid his head on Stiles chest, the both of them trying to catch their breath. 

After a couple minutes pass, Derek pulls out carefully and takes off the condom, tying it off and tossing it into the small wastebasket near the bed before getting up and disappearing into the bathroom. Stiles can hear the faucet turning on as he takes the lube covered pillow out from under him and tosses it on the floor as Derek comes back into the room with a wet washcloth. 

Stiles lets Derek wipe the cum and lube off him, Derek doing the same thing to himself before tossing the washcloth into a laundry basket and lying down beside Stiles. 

Stiles immediately throws his arm and leg over Derek, his head resting on his chest. “Would it be tacky if I go to sleep right after sex?” he mumbled, drowsy. 

Derek chuckled and nodded his head, wrapping his arms around his boyfriend. “Yes, but I promise not to hold it against you.” 

Stiles snorted and shut his eyes. 

“‘Night, Der.” 

“Goodnight, Stiles.” 

**Notes for the Chapter:**

> [follow my personal tumblr](http://cursed-kid.tumblr.com)   
>  [fandom tumblr](http://hecks-eyebrows.tumblr.com)   
>  [my beta's tumblr](http://sassyhunters.tumblr.com)


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